The achievement says 5 rolls in one crash. Crash. So methinks you have to start the jump like a crash, basically take damage and then roll. As I've noticed some people just think they have to do 5 rolls from a barrel roll or a jump. I haven't had time to test this out, but when I got it I used the little yellow airport ramps, if you just do it like a barrel roll at full speed, it should count as a crash from the way the car hits the ramp, then doing the five rolls should earn you the achievement. I also had a problem, I done like 6 or 7 rolls, but thinking back, I don't recall taking any damage until I landed.

It's known that this Achievement is massively flawed as most people have experienced. I've gotten 6/7/8 rolls and nothing btu did only 3 and got the Achievement. There's no set way, it's just try, try and try again really.

This achievement really has me, tried for hours n replicated sme others i have seen on youtube videos but still cant manage 5 rolls. Anyone know a gd way of getting it besides what i already no (airport, not lowered car etc.). im finding that if you turn away from the ramp slighly just as u hit it it works slightly better but its still not rolling 5 times.

got it today with a police patriot at the airport
i think i had the same issue as others i rolled a bunch of times (more than 5) and didnt get shit but then soon after i rolled maybe 3 times? and i got the acheivement